Abstract
Different malonaldehyde-amine condensation products were tested for their relative color contribution to the thiobarbituric acid (TBA) test, an indicator for oxidative rancidity of polyunsaturated lipids. The open chain mono- and disubstituted malonaldehyde (M) addition products (R-N=CH-CH=CHOH and R-N=CH-CH=CH-NH-R) gave complete (100%) recovery ofM on a mole basis. When theM residue was incorporated into cyclic products which formed between the ureido- or guanidino- substituents of α-amino acids such as citrulline or arginine andM, recovery ofM by the TBA color test was 30% and 6%, respectively. Products, from imine-amine type interactions, containing theM residue as in pyrazoline or pyrazole ring systems, released from 4% to noM.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Sinnhuber, R.O., T.C. Yu and T.E. Chang Yu, Food Res. 23: 626 (1958).
Kwon, T.W., and H.S. Olcott, Nature 210: 214 (1966).
Dillard, C.J., and A.L. Tappel, Lipids 6: 715 (1971).
Chipault, J.R., and J.M. Hawkins, J. Agr. Food Chem. 19: 495 (1971).
Holland, D.C. J. Ass. Offic. Anal. Chem. 54: 1024 (1971).
King, T.P., Biochemistry 5: 3454 (1966).
Protopopova, T.V., and A.P. Skoldinov, J. Gen. Chem. USSR 28: 1360 (1958).
Hüttel, R., Ber. 74: 1825 (1941).
Saslaw, L.D., and V.S. Waravdekar, J. Org. Chem. 22: 843 (1957).
Buttkus, H., and R.J. Bose, Ibid. 36: 3895 (1971).
Crawford, D.L., T.C. Yu and R.O. Sinnhuber, J. Agr. Food Chem. 14: 182 (1966).
Buttkus, H., JAOCS 46: 88 (1969).
Chio, K.S., and A.L. Tappel, Biochemistry 8: 2821 (1969).
George, W.O., and V.G. Mansell, J. Chem. Soc. B. 132 (1968).
Harada, K., in “The Chemistry of the Carbon-Nitrogen Double Bond,” Interscience Publishers, London, 1970, p. 255.
Dudek, G.O., and E.P. Dudek, J. Amer. Chem. Soc. 88: 2407 (1966).
Bovey, F.A., “Nuclear Magnetic Resonance,” Academic Press, New York, 1969.
Perlin, A.S., Can. J. Chem. 44: 539 (1966).
Perrin, D.D., and I.H. Pitman, Aust. J. Chem. 18: 763 (1965).
Author information
Authors and Affiliations
About this article
Cite this article
Buttkus, H., Bose, R.J. Amine-malonaldehyde condensation products and their relative color contribution in the thiobarbituric acid test. J Am Oil Chem Soc 49, 440–443 (1972). https://doi.org/10.1007/BF02582530
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02582530